Monomethyl terephthalate → Methyl 4-(pyrrolidine-1-carbonyl)benzoate

HRID 1093798Notes

Reaction equation

HRID 1093798 reaction equation
CC[N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.[CH3:10][O:11][C:12](=[O:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.N1CCCC1>CN(C=O)C.O>[CH3:10][O:11][C:12](=[O:22])[C:13]1[CH:14]=[CH:15][C:16]([C:17]([N:3]2[CH2:4][CH2:6][CH2:9][CH2:7]2)=[O:19])=[CH:20][CH:21]=1

Participants

8

Reactant 5

HCID 15513Monomethyl terephthalateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 17178210Methyl 4-(pyrrolidine-1-carbonyl)benzoateYield 81.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (1.26 g, 9.7 mmol) was added to a stirred solution of terephthalic acid monomethyl ester (500 mg, 2.77 mmol) in DMF (3 mL) followed by HOBt (410 mg, 3.0 mmol) and EDCI (1.32 g, 7.0 mmol). After 2 minutes of stirring, pyrrolidine (215 mg, 3.0 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected to afford 53 mg (81.9% Yield) of 4-(pyrrolidine-1-carbonyl)-benzoic acid methyl ester. LiOH.H2O (285 mg, 6.8 mmol) was added to a solution of 4-(pyrrolidine-1-carbonyl)-benzoic acid methyl ester (530 mg, 2.27 mmol) in a mixture of methanol (2 mL), THF (6 mL) and H2O (2 mL). The reaction mixture was stirred at ambient temperature for 3 hrs. The reaction mixture was concentrated, the residue was diluted with water, and acidified with conc. HCl. The solid was filtered and dried to afford 41 mg (82.32% Yield).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customthe precipitate was collected

Sources & evidence

ORD record
ord-40a1f3062e574f39a4f6700f1f96486f
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

Loading…